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Published on: January 15, 2012
Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ6 -α-Iodoketone
Milos Trajkovic1, Zorana Ferjancic1, Radomir N Saicic1,2
1Faculty of Chemistry, University of Belgrade, Studentski trg 16, POB 51, 11158, Belgrade 118, Serbia.
Abstract:
A chiral-pool-based synthesis of the platensimycin core was achieved using (S)-lactic acid as an inexpensive starting material. The cyclohexenone ring was closed in a Mukaiyama-Michael domino sequence, while the quaternary stereocenter was created by a highly stereoselective decarboxylative allylation. The spirobicyclic skeleton was constructed by a RCM reaction. A new silver(I)-promoted cyclization reaction of Δ6 - and Δ7 -α-iodoketones was developed and applied for the pivotal carbon-carbon bond formation. The scope and limitations of this methodology are also presented.
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